Tetrabutylammonium Fluoride → 4-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

Participants

Reaction Steps

To a solution of 4-methyl-4-trimethylsilanyloxy-pent-2-ynoic acid ethyl ester (5.4 g, 23.7 mmol) in ethyl ether (50 mL) was added tetrabutylammonium fluoride (TBAF) (7.42 g, 28.4 mmol). The reaction mixture was stirred at room temperature for 2 hours, quenched with H2O, and extracted with ethyl ether. The organic phase was washed with brine, dried (Na2SO4) and concentrated to afford 3.51 g of 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester as yellow oil.

Provenance & Evidence